This invention relates to a process, and the catalyst which achieves this process, for making alcohols from synthesis gas, i.e., mixtures of hydrogen and carbon monoxide. More particularly the invention relates to the reaction of an organosilicon compound in the presence of a catalyst which is a ruthenium carbonyl complex wherein said organosilicon compound has at least one substituent such that the substituent-silicon bond will add across a transition metal, e.g. hydrogen bonded to silicon, and a carbon residue R--.
Earlier relevant studies fall into the categories of: (1) "insertion" of a transition metal into a Si--C bond (cleavage of a Si--C bond by a transition metal) and (2) "insertion" of a carbonyl unit into a Si--C bond.
The general potential of a transition metal compound to cleave the silicon-carbon bond in an organosilicon compound has been discussed by I. S. Akhrem, D. V. Avetisyan, R. S. Vartanyan, K. G. Shakhatuni, and M. E. Vol'pin, Izv. Akad. Nauk SSSR, 2327 (1975).
The reaction of iron carbonyls with silicon hetercycles, for example: ##STR1## has been reported by C. S. Cundy, M. F. Lappert, J. Dubac, and P. Mazerolles, J. C. S. Dalton, 910 (1976); C. S. Cundy and M. F. Lappert, Chem. Comm., 445 (1972); and C. S. Cundy and M. F. Lappert, J. C. S. Dalton, 665 (1978). No reaction with Fe.sub.2 (CO).sub.9 was observed when the silicon heterocycle was ##STR2## Further, no transition metal-silicon complex was isolated from the attempted reaction of the silacyclobutane and metal complexes of Cr, Mo, Mn, Ru, Co, Pt, Ir and Zr wherein, in most cases, no appreciable reaction was reported to have occurred.
Also, ##STR3## did not react with H.sub.2 or CO in benzene up to reflux temperature.
The reaction: ##STR4## was reported by C. S. Cundy and M. F. Lappert, J. Organometal. Chem., 144, 317 (1978). Further, C. S. Cundy, C. Eaborn, and M. F. Lappert, J. Organometal. Chem., 44, 291 (1972) reported a study on polymerization of organosilanes and proposed the reaction: ##STR5## wherein R=X and is CH.sub.3, --OCH.sub.3 or R=CH.sub.3 when X is Cl.
The reaction: ##STR6## was reported by O. V. Kuz'min, A. L. Bykovets, V. M. Vdovin, and A. M. Krapavin, Izv. Akad. Nauk SSSR, 2815 (1979).
The cleavage of the silicon/carbon bond in organosilicon compounds by compounds of the platinum group metals Pt, Rh, Pd, Ru, Os and Ir were studied and reported by I. S. Akhrem, R. S. Vartanyan, N. M. Chistovalova, E. I. Mysov and M. E. Vol'pin, Izv. Akad. Nauk SSSR, 2069 (1976); I. S. Akhrem, N. M. Chistovalova, E. I. Mysov, and M. E. Vol'pin, Zh. Obshch. Khim, 42, 1868 (1972). The reaction of (CH.sub.3).sub.4 Si, (CH.sub.3).sub.3 Si(C.sub.2 H.sub.5), (CH.sub.3).sub.3 SiC.sub.4 H.sub.9 and (CH.sub.3).sub.3 Si(C.sub.6 H.sub.5) were studied and cleavage of the silicon-carbon bond observed.
The palladium-catalyzed addition of an organosilicon compound: ##STR7## to alkynes and a diene to give an addition product has been reported by D. Seyferth, S. C. Vick, M. C. Shannon, T. F. O. Lim, and D. P. Duncan, J. Organometal, Chem., 135, C37 (1977). Exemplary of the addition reaction reported therein is: ##STR8## wherein R is (CH.sub.3).sub.3 C or CH.sub.3 C.dbd.CH.sub.2. Similarly, where R is C.sub.6 H.sub.5 was reported by D. Seyferth, D. P. Duncan, and S. C. Vick, J. Organometal. Chem, 125, C5 (1977).
For additional reports of the cleavage of a Si--C bond by a transition metal, see H. Sakurai, Y. Kamiyama, and Y. Nakadaira, J. Am. Chem. Soc., 99, 3879 (1977); M. Ishikawa, T. Fuchikami, and M. Kumada, Chem. Comm., 352 (1977); D. Mansuy, J. F. Bartoli, and J. C. Chottard, J. Organometal. Chem., 77, C49(1974); D. Mansuy, J. Pusset, and J. C. Chottard, J. Organometal. Chem., 105, 169 (1976); D. Mansuy, J. F. Bartoli, and J. C. Chottard, J. Organometal. Chem., 71, C32 (1974); I. S. Akhrem, N. M. Chistovalova, E. I. Mysov, and M. E. Vol'pin, J. Organometal. Chem., 72, 163 (1974); J. M. Kliegman, J. Organometal. Chem., 29, 73 (1971); C. G. Pitt and K. R. Skillern, J. Organometal, Chem., 7, 525 (1967); K. R. Beck and R. A. Benkeser, J. Organometal. Chem., 21, P35 (1970); D. R. Wegenberg and L. E. Nelson, J. Org. Chem., 30, 2618 (1965); M. R. Stober, M. C. Musolf, and J. L. Speier, J. Org. Chem., 30, 1651 (1965); E. M. Haschke and J. W. Fitch, J. Organometal. Chem., 57, C93 (1973); H. Gilman and D. H. Miles, J. Org. Chem., 23, 326 (1958); J. E. Poist and C. S. Krainhanzel, Chem. Comm., 607 (1968); N. S. Nametkin, V. M. Vdovin, and P. L. Grinberg, Izv. Akad. Nauk SSSR, 1133 (1964); W. P. Weber, R. A. Felix, A. K. Willard, and K. E. Koenig, Tet. Lett., 4701 (1971); I. S. Akhrem, N. M. Chistovalova, S. M. Airapetyan, E. I. Mysov, and M. E. Vol'pin, Izv. Akad. Nauk SSSR, 1126 (1978); J.-i. Yoshida, K. Tamao, M. Takahashi, and M. Kumada, Tet. Lett., 2161 (1978); I. S. Akhrem, D. V. Avetisyan, R. S. Vartanyan, K. G. Shakhatuni, and M. E. Vol'pin, Izv. Akad. Nauk SSSR, 2327 (1975).
In the category of "insertion" of a carbonyl unit into a Si--C bond, D. Seyferth, D. P. Duncan, and S. C. Vick, J. Organometal. Chem., 125, C5 (1977) reported the reaction: ##STR9## wherein R is phenyl and R' is methyl. Similarly, D. Seyferth, S. C. Vick, M. L. Shannon, T. F. O. Lim and D. P. Duncan, J. Organometal Chem., 135, C37 (1977) reported the reactions: ##STR10## wherein R is H or CH.sub.3 ; R' is CH.sub.3.
E. W. Abel and R. J. Rowley, J. Organometal. Chem., 84, 199 (1975) reported the reaction: ##STR11##
The insertion of a carbonyl unit into the silicon-carbon bond of ##STR12## has been reported by H. Sakurai, Y. Kamiyama and Y. Nakadaira, J. Am. Chem. Soc., 99, 3879 (1977).
R. Calas, J. Dunogues, G. Deleris, and F. Pisciotti, J. Organometal. Chem., 69, C15 (1974); and G. Deleris, J. Dunogues and R. Calas, J. Organometal. Chem., 93, 43 (1975) generally report the reaction of carbonyl containing compounds and organosilicon compounds. For example: ##STR13## wherein R=CCl.sub.3, R'=H; R=CH.sub.3, R'=CH.sub.2 Cl.
For additional examples of the "insertion" of a carbonyl group into a Si--C bond see B. A. Gostevskii, O. A. Kruglaya, A. I. Albanov, and N. S. Vyazankin, J. Organometal. Chem., 187, 157 (1980) and the references cited therein.
The above discussion provides a brief characterization of the technology heretofore published or filed upon which relates to the hydroxymethylation of a carbon residue bonded to a silicon atom. The instant process is to be distinguished from the aforementioned processes in that there has been no previous report of the hydroxymethylation of a carbon residue bonded to a silicon atom nor has there been a report of the insertion of CO into such a silicon-carbon bond. The source of the carbonyl group in the instant process is carbon monoxide and is generally derived from synthesis gas. Synthesis gas is a source of such carbonyl groups that can be produced from non-petroleum sources.